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Hydrochloric acid (35%) (3.2 L) was added to a cooled solution of 4-aminobenzamide (2.0 Kg, 14.69 mol) in water (14 L, 7 volumes) at 5-100C. Then p-toluene sulphonic acid (10.1 Kg, 3.44 mol) was added to the reaction mixture and further cooled to -5C to -100C. Sodium nitrite (1.76 Kg, 25.7 mol) was dissolved into water (4 L, 2 volumes) and added to the cooled reaction mixture over a period of 2.5 hours at -5C to -100C and further stirred for 4 hours. Sodium sulphite (5.6 Kg, 44.4 mol) was dissolved into water (16 L, 8 volumes) and added dropwise to the diazonium salt over a period of 3 hours at a temperature of -5C to -100C. After stirring for 2 hours, the temperature of the reaction mixture was allowed to rise to ambient and stirred for 12 hours. The reaction was monitored by TLC. Methanol (16 L, 8 volumes) was added to the yellow suspension and 4-phthalimido- cyclohexanone (4.64 Kg, 19.07 mol) was added portionwise at a temperature of 40-450C. After maintaining the reaction mixture at 40-450C for 30 minutes, the temperature of the reaction mixture was raised to 70-750C and maintained for 8 hours. After completion of the reaction, the mixture was cooled to 25-300C, filtered and washed with water (40 L). The wet cake was mixed with water (40 L) and the pH adjusted to 7-8 using 10% potassium carbonate (aq) solution, and the slurry was filtered and washed with water (40 L). The product was dried under vacuum at 60-650C. The crude product was purified by reflux in dichloromethane (30 L) and dried to afford the title compound (3.70 Kg). Molar yield: 70%HPLC purity: 98.06%
Dissolved 0.500 g <strong>[17823-69-7]2-cyano-3,3-bis(methylthio)acrylamide</strong> in 15 mL EtOH and added 4-Aminobenzamide (1.0 eq.) . Stirred reaction at 75 C until starting amide was absent by HPLC. Once complete (18 hrs), reaction was brought to room temperature and filtered to obtain a light yellow powder as product. Product was allowed to dry under vacuum for 1 hr. Product was then suspended in 10 mL EtOH and hydrazine hydrate (1 eq.) was added dropwise. Reaction was heated at 75 C until intermediate was absent (HPLC). Once intermediate was absent (18 hrs), reaction was brought to room temperature and filtered to obtain 5-amino-3-((4-carbamoylphenyl)amino)-lH-pyrazole-4-carboxamide as a a yellow powder. Product was allowed to dry under vacuum for 1 hr. 5-amino-3-((4-carbamoylphenyl)amino)-lH-pyrazole-4-carboxamide
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